405150-20-1

Basic information

• Product Name: S-(2-THIAZOLYL)-L-CYSTEINE
• Synonyms: purum,NLT95+%byHPLC
• CAS NO: 405150-20-1
• Molecular Formula: C6H8N2O2S2
• Molecular Weight: 204.27
• Mol File: 405150-20-1.mol

Chemical Properties

• Boiling Point: 397.425°C at 760 mmHg
• Flash Point: 194.156°C
• Appearance: /
• Density: 1.508g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.657
• Storage Temp.: 2-8°C
• CAS DataBase Reference: S-(2-THIAZOLYL)-L-CYSTEINE(CAS DataBase Reference)
• NIST Chemistry Reference: S-(2-THIAZOLYL)-L-CYSTEINE(405150-20-1)
• EPA Substance Registry System: S-(2-THIAZOLYL)-L-CYSTEINE(405150-20-1)

Safety Data

• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 405150-20-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
S-(2-THIAZOLYL)-L-CYSTEINE is used as a key intermediate in the semisynthetic production of unnatural L-α-amino acids. These unnatural amino acids are valuable for the development of novel pharmaceutical compounds with improved properties, such as enhanced stability, selectivity, and bioavailability. The incorporation of S-(2-THIAZOLYL)-L-CYSTEINE into drug molecules can lead to the creation of innovative therapeutic agents with potential applications in the treatment of various diseases and conditions.
Used in Metabolic Engineering Research:
S-(2-THIAZOLYL)-L-CYSTEINE serves as a valuable tool in the field of metabolic engineering, where it can be used to study the biosynthetic pathways of amino acids and other related metabolites. By manipulating the cysteine-biosynthetic pathway, researchers can gain insights into the regulation and optimization of these pathways, potentially leading to the development of more efficient and sustainable methods for the production of amino acids and their derivatives.
Used in Chemical Synthesis:
The unique structure of S-(2-THIAZOLYL)-L-CYSTEINE makes it an attractive building block for the synthesis of various organic compounds, including complex natural products and bioactive molecules. Its thiazolyl group can participate in a range of chemical reactions, such as cycloadditions, cross-couplings, and electrophilic substitutions, enabling the construction of diverse molecular frameworks with potential applications in the fields of material science, agrochemistry, and medicinal chemistry.

InChI:InChI=1/C6H8N2O2S2/c7-4(5(9)10)3-12-6-8-1-2-11-6/h1-2,4H,3,7H2,(H,9,10)/t4-/m0/s1

Upstream product

• 407-41-0 L-phosphoserine 
• 5685-05-2 2-mercaptothiazole 
• 5147-00-2 O-acetyl-L-serine 

Downstream Products

• 1426207-73-9 C₁₆H₁₈N₂O₃S₂ 

Relevant articles and documents

Expanding the Structural Diversity of Protein Building Blocks with Noncanonical Amino Acids Biosynthesized from Aromatic Thiols

Incorporation of structurally novel noncanonical amino acids (ncAAs) into proteins is valuable for both scientific and biomedical applications. To expand the structural diversity of available ncAAs and to reduce the burden of chemically synthesizing them, we have developed a general and simple biosynthetic method for genetically encoding novel ncAAs into recombinant proteins by feeding cells with economical commercially available or synthetically accessible aromatic thiols. We demonstrate that nearly 50 ncAAs with a diverse array of structures can be biosynthesized from these simple small-molecule precursors by hijacking the cysteine biosynthetic enzymes, and the resulting ncAAs can subsequently be incorporated into proteins via an expanded genetic code. Moreover, we demonstrate that bioorthogonal reactive groups such as aromatic azides and aromatic ketones can be incorporated into green fluorescent protein or a therapeutic antibody with high yields, allowing for subsequent chemical conjugation.

Unnatural amino acid synthesis by thermostable O-phospho-L-serine sulfhydrylase from hyperthermophilic archaeon Aeropyrum pernix K1

O-Acetyl-L-serine sulfhydrylase (OASS) from plants and bacteria synthesizes cysteine and unnatural amino acids that are important building blocks for active pharmaceuticals and agrochemicals. A thermostable O-phospho-L-serine sulfhydrylase from hyperthermophilic archaeon Aeropyrum pernix K1 (OPSSAp) exhibits a function similar to OASS. In the present study, we examined the synthesis of various unnatural amino acids using OPSSAp and demonstrated OPSSAp could efficiently synthesize various sulfur-containing amino acids. OPSSAp would be useful for industrial production of biologically important unnatural amino acids.